In this article, we outline a model of how organizations can effectively shape employees’ affective reactions to failure. We do not suggest that organizations eliminate the experience of negative affect following performance failures—instead, we propose that they encourage a more constructive form of negative affect (guilt) instead of a destructive one (shame). We argue that guilt responses prompt employees to take corrective action in response to mistakes, whereas shame responses are likely to elicit more detrimental effects of negative affect. Furthermore, we suggest that organizations can play a role in influencing employees’ discrete emotional reactions to the benefit of both employees and the organization. We describe the necessary antecedents for encouraging guilt responses without simultaneously eliciting shame. In essence, employees are more likely to experience guilt (but not shame) if they feel they had control over a specific negative event and the event resulted in a negative outcome for others. Given these necessary preconditions, we identify a set of organizational characteristics—autonomy, specificity of performance feedback, and outcome interdependence—that can be modified to make the experience of guilt more likely than that of shame in the workplace. The ethical and practical limits of shaping employees’ emotional experiences within a negative affective domain are also addressed.